Guaianolides from Ormenis mixta: Structural Insights and Evaluation of Their Anti-inflammatory Profile

Benteldjoune, Mounira; Chini, Maria Giovanna; Iannuzzi, Anna Maria; Kabouche, Ahmed; Kabouche, Zahia; DʼAmbola, Massimiliano; Marzocco, Stefania; Autore, Giuseppina; Bifulco, Giuseppe; Tommasi, Nunziatina De

doi:10.1055/a-0941-0364

Cited by 6 publications

(4 citation statements)

References 25 publications

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“…Compound 2 (C 15 H 20 O 6 ) displayed a sodiated molecular ion at m / z 319.1155 [M + Na] + , requiring six hydrogen deficiencies. Its NMR features suggested the presence of a guaianolide sesquiterpene. , The NMR spectra (Table ) showed the presence of two methyls, two methylenes (one olefinic), four methines (two olefinic), two hydroxymethines, three oxygenated tertiary carbons, one quaternary carbon, and a lactone group. 1D TOCSY, COSY, and HSQC experiments were useful to establish the spin systems, H-5–H-9 and H-6–H 2 -13, included in an α-methylene-γ-lactone unit.…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Sesquiterpenoids from Ammoides atlantica Aerial Parts

et al. 2022

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Seven new terpenoids, namely, guaiane ( 1 – 4 ), eudesmane ( 5 ), and bisabolane ( 6 ) sesquiterpenoids and a furanone ( 7 ), were isolated from the aerial parts of Ammoides atlantica , a herbaceous plant growing in Algeria, together with eight known compounds. All metabolites were characterized by their 1D and 2D NMR and HRESIMS data. A combined DFT/NMR method was applied to study the relative configurations of 1 – 4 , 6 , and 7 . All compounds, except 2 , were assayed against MCF-7, A375, A549, HaCaT, and Jurkat cell lines. Compounds 8 , 10 , and 11 induced a dose-dependent reduction in cell viability with different potency on almost all cell lines used. The most active compounds, 8 and 10 , were studied to assess their potential apoptotic effects and cell cycle inhibition.

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Section: Resultsmentioning

confidence: 99%

Cytotoxic Sesquiterpenoids from Ammoides atlantica Aerial Parts

et al. 2022

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“…Phytochemical investigation of the non-volatile constituents of Cladanthus species indicated the occurrence of flavonoids and phenolic acids in the extracts of C. arabicus [21] and C. mixtus [22,23], poliacetylenes in C. arabicus [24], coumarins in C. mixtus [25], and sesquiterpenes in C. mixtus [26] and C. arabicus [27]. Apart from C. flahaultii, which is totally devoid of any investigation, all the other four taxa have been studied for the composition of their essential oils (EOs) and for some biological activities as reported in Table 2.…”

Section: Moroccomentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cladanthus scariosus Essential Oil and Its Principal Constituents with Cytotoxic Effects on Human Tumor Cell Lines

Badalamenti,

Ilardi,

Bruno

et al. 2024

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Cladanthus is a small genus of the Asteraceae family comprising just five species that, apart from Cladanthus mixtus (L.) Chevall., has a large distribution in all the Mediterranean countries, mainly in the North Africa area. Several ethnopharmacological uses have been reported for species of this genus. Notably, Cladanthus scariosus (Ball) Oberpr. & Vogt is endemic to Morocco. Seeking to delve deeper into the phytochemistry and pharmacological aspects of this species, in this work, we investigated the essential oil (EO) obtained from the aerial parts of a locally sourced accession, hitherto unexplored, growing wild near Tizi n’Ticha, Morocco. The chemical composition of the EO, obtained by the hydrodistillation method, was evaluated by GC and GC-MS. The most abundant EO constituent was germacrene D (13.2%), the principal representative of the sesquiterpene hydrocarbons class (27.2%). However, the major class of constituents was monoterpene hydrocarbons (43.0%), with α-pinene (11.9%), sabinene (10.2%), p-cymene (8.5%), and α-phellandrene (5.2%) as the most abundant. The EO and its main constituents have been tested for their possible cytotoxic activity against three human tumor cell lines (MDA-MB 231, A375, and CaCo2) using the MTT assay, with corresponding IC50 values of 13.69, 13.21, and 22.71 µg/mL, respectively. Germacrene D and terpinen-4-ol were found to be the most active constituents with IC50 values between 3.21 and 9.53 µg/mL. The results demonstrate remarkable cytotoxic activity against the three human tumor cell lines studied, and in the future, further analyses could demonstrate the excellent potential of C. scariosus EO as an antitumor agent.

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“…Guaianolides recently isolated from Ormenis mixta L. and characterized as 2,3-epoxy-1,4,10-trihydroxyguaian-12,6α-olide diastereoisomers, revealed an anti-inflammatory potential through the inhibition of NO release and COX-2 expression in murine macrophages treated with LPS [ 49 ].…”

Section: Anti-inflammatory Potential Of Sesquiterpene Lactonesmentioning

confidence: 99%

Sesquiterpene Lactones: Promising Natural Compounds to Fight Inflammation

2021

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Inflammation is a crucial and complex process that reestablishes the physiological state after a noxious stimulus. In pathological conditions the inflammatory state may persist, leading to chronic inflammation and causing tissue damage. Sesquiterpene lactones (SLs) are composed of a large and diverse group of highly bioactive plant secondary metabolites, characterized by a 15-carbon backbone structure. In recent years, the interest in SLs has risen due to their vast array of biological activities beneficial for human health. The anti-inflammatory potential of these compounds results from their ability to target and inhibit various key pro-inflammatory molecules enrolled in diverse inflammatory pathways, and prevent or reduce the inflammatory damage on tissues. Research on the anti-inflammatory mechanisms of SLs has thrived over the last years, and numerous compounds from diverse plants have been studied, using in silico, in vitro, and in vivo assays. Besides their anti-inflammatory potential, their cytotoxicity, structure–activity relationships, and pharmacokinetics have been investigated. This review aims to gather the most relevant results and insights concerning the anti-inflammatory potential of SL-rich extracts and pure SLs, focusing on their effects in different inflammatory pathways and on different molecular players.

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Guaianolides from Ormenis mixta: Structural Insights and Evaluation of Their Anti-inflammatory Profile

Cited by 6 publications

References 25 publications

Cytotoxic Sesquiterpenoids from Ammoides atlantica Aerial Parts

Cytotoxic Sesquiterpenoids from Ammoides atlantica Aerial Parts

Cladanthus scariosus Essential Oil and Its Principal Constituents with Cytotoxic Effects on Human Tumor Cell Lines

Sesquiterpene Lactones: Promising Natural Compounds to Fight Inflammation

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